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MDW - PUJ

$104 Find cheap flights from Chicago Midway Airport to Punta Cana

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from Midway to Punta Cana departing on 8/10. Fares are subject to change and may not be available on all flights or dates of travel. Click the price to replicate the search for this deal.
1 adult
0 bags
Sun 6/30
Sun 7/7

Search hundreds of travel sites at once for deals on flights to Punta Cana

 
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Chicago to Punta Cana, as well as popular online travel agencies
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Chicago to Punta Cana, as well as popular online travel agencies
In the last 7 days travelers have searched 42,686,544 times on KAYAK, and here is why:

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Cheap flight deals from Midway to Punta Cana (MDW-PUJ)

Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Midway to Punta Cana that are departing in the next months. While these flights were available on KAYAK in the last 72 hours, prices and availability are subject to change and deals may expire.
Discover the best prices and deals for you by selecting your travel dates.
Choose your dates
5:14 pm - 9:28 amMDW-PUJ
15h 14m1 stop
10:33 am - 7:31 amPUJ-MDW
21h 58m1 stop
$216Frontier
Find Deal
Mon, Jun 24 - Thu, Jun 27
5:14 pm - 9:28 amMDW-PUJ
15h 14m1 stop
10:33 am - 7:31 amPUJ-MDW
21h 58m1 stop
$217Frontier
Find Deal
Mon, Jun 24 - Thu, Jun 27
6:05 pm - 10:31 amMDW-PUJ
15h 26m1 stop
10:52 am - 12:20 amPUJ-MDW
14h 28m1 stop
$221Frontier
Find Deal
Tue, Jun 25 - Thu, Jun 27
9:31 am - 9:20 amMDW-PUJ
22h 49m1 stop
10:07 am - 9:45 amPUJ-MDW
24h 38m1 stop
$226Frontier
Find Deal
Mon, Jul 8 - Sat, Jul 13
8:53 pm - 3:42 pmMDW-PUJ
17h 49m1 stop
10:33 am - 7:31 amPUJ-MDW
21h 58m1 stop
$228Frontier
Find Deal
Sun, Jun 23 - Thu, Jun 27
5:14 pm - 9:28 amMDW-PUJ
15h 14m1 stop
6:10 pm - 7:31 amPUJ-MDW
14h 21m1 stop
$236Frontier
Find Deal
Mon, Jun 24 - Tue, Jun 25
2:54 pm - 3:41 pmMDW-PUJ
23h 47m1 stop
11:17 am - 7:18 pmPUJ-MDW
9h 01m1 stop
$238Frontier
Find Deal
Thu, Sep 5 - Mon, Sep 9
1:50 pm - 1:02 pmMDW-PUJ
22h 12m2 stops
6:47 pm - 8:36 amPUJ-MDW
14h 49m1 stop
Tue, Jul 2 - Tue, Jul 9
5:45 pm - 12:49 pmMDW-PUJ
18h 04m2 stops
3:04 pm - 8:38 amPUJ-MDW
18h 34m2 stops
$440Delta
Find Deal
Sat, Aug 31 - Sat, Sep 7
5:59 pm - 12:36 pmMDW-PUJ
17h 37m2 stops
4:23 pm - 8:45 amPUJ-MDW
17h 22m2 stops
$484Delta
Find Deal
Wed, Oct 23 - Wed, Oct 30

Flights from Midway to Punta Cana - Travel Insights & Trends

Get data-powered insights and trends into flights from Midway to Punta Cana to help you find the cheapest flights, the best time to fly and much more.

What is the cheapest month to fly from Chicago Midway Airport to Punta Cana?

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for flights from Chicago Midway Airport to Punta Cana, removes the top 0.1% to account for outliers, and then takes the median of all values for each month.
The cheapest month for flights from Chicago Midway Airport to Punta Cana is April, where tickets cost $458 on average. On the other hand, the most expensive months are March and June, where the average cost of tickets is $704 and $593 respectively.

How far in advance should I book a flight from Chicago Midway Airport to Punta Cana?

To calculate daily average prices, KAYAK takes all prices for each day before departure over the last year for flights from Chicago Midway Airport to Punta Cana, removes the top 0.1% to account for outliers, and then takes the average of all the values for each month.
To get a below average price on the flight from Chicago Midway Airport to Punta Cana, you should book around 1 day before departure. For the absolute cheapest price, our data suggests you should book 15 days before departure.

Which airlines provide the cheapest flights from Chicago Midway Airport to Punta Cana?

The cheapest price for the route for each airline clicked by KAYAK users in the last 72 hours.
The best deals for a one-way ticket found by KAYAK users over the last 3 days were on Frontier ($104) and Delta ($206). The cheapest round-trip tickets were found on Frontier ($216) and Delta ($440).

How many flights are there between Chicago Midway Airport and Punta Cana per day?

There is a maximum of 1 nonstop flight a day that takes off from Chicago Midway Airport and lands in Punta Cana, with an average flight time of 4h 35m. The most common departure time is 8:00 am and most flights take off in the morning. Each week, there are 7 flights.

What’s the earliest departure time from Chicago Midway Airport to Punta Cana?

Early birds can take the earliest flight from Chicago Midway Airport at 8:20 am and will be landing in Punta Cana at 1:55 pm.

What’s the latest departure time from Chicago Midway Airport to Punta Cana?

If you prefer to fly at night, the latest flight from Chicago Midway Airport to Punta Cana jets off at 9:55 am and lands at 3:25 pm.

Good to know

Low season

April

High season

February

Cheapest flight

$104
Best time to beat the crowds with an average 19% drop in price.
Most popular time to fly with an average 31% increase in price.
Flight from Chicago Midway Airport to Punta Cana

When to book flights from Midway to Punta Cana

Are your dates flexible? Find out the best times to travel from Midway to Punta Cana based on our flight data from the last year. Discover the cheapest month and even day to fly.
Estimated round-trip price
KAYAK looks at all historical flight data for each date to provide a predicted price for one-way trips or round-trips with a duration up to 40 days. While we try to provide actual minimum prices for each date, some prices are predictions and actual prices may differ.

FAQs for booking Chicago Midway Airport to Punta Cana flights

  • What is the cheapest flight from Chicago Midway Airport to Punta Cana?

    In the last 3 days, the lowest price for a flight from Chicago Midway Airport to Punta Cana was $104 for a one-way ticket and $216 for a round-trip.

  • Do I need a passport to fly between Chicago Midway Airport and Punta Cana?

    A passport is required to fly from Chicago Midway Airport to Punta Cana.

  • Which aircraft models fly most regularly from Chicago Midway Airport to Punta Cana?

    We unfortunately don’t have that data for this specific route.

  • On which days can I fly direct from Chicago Midway Airport to Punta Cana?

    There are nonstop flights from Chicago Midway Airport to Punta Cana on a daily basis.

  • Which is the best airline for flights from Chicago to Punta Cana, Delta or Frontier?

    The two airlines most popular with KAYAK users for flights from Chicago to Punta Cana are Delta and Frontier. With an average price for the route of $801 and an overall rating of 8.0, Delta is the most popular choice. Frontier is also a great choice for the route, with an average price of $472 and an overall rating of 6.2.

  • How does KAYAK find such low prices on flights from Chicago Midway Airport to Punta Cana?

    KAYAK is a travel search engine. That means we look across the web to find the best prices we can find for our users. With over 2 billion flight queries processed yearly, we are able to display a variety of prices and options on flights from Chicago Midway Airport to Punta Cana.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Chicago Midway Airport to Punta Cana?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Punta Cana from Chicago Midway Airport is likely to change within 7 days, so travelers know whether to wait or book now.

  • What is the Hacker Fare option on flights from Chicago Midway Airport to Punta Cana?

    Hacker Fares allow you to combine one-way tickets in order to save you money over a traditional round-trip ticket. You could then fly to Punta Cana with an airline and back to Chicago Midway Airport with another airline. Booking your flights between Chicago Midway Airport and PUJ can sometimes prove cheaper using this method.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Chicago Midway Airport to Punta Cana?

    Sometimes travel dates aren't set in stone. If your preferred travel dates have some wiggle room, flexible dates will show you all the options when flying to Punta Cana from Chicago Midway Airport up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

See more FAQs

Prefer to fly non-stop from Chicago Midway Airport to Punta Cana?

Find which airlines fly direct from Midway to Punta Cana, which days they fly and book direct flights.

Nonstop departures

Chicago Midway to Punta Cana

Monday

Southwest

Southwest

Tuesday

Southwest

Southwest

Wednesday

Southwest

Southwest

Thursday

Southwest

Southwest

Friday

Southwest

Southwest

Saturday

Southwest

Southwest

Sunday

Southwest

Southwest

See more direct flights

Nonstop returns

Punta Cana to Chicago Midway

Monday

Southwest

Southwest

Tuesday

Southwest

Southwest

Wednesday

Southwest

Southwest

Thursday

Southwest

Southwest

Friday

Southwest

Southwest

Saturday

Southwest

Southwest

Sunday

Southwest

Southwest

See more direct flights
See more direct flights

Top 3 airlines serving from Midway to Punta Cana

 
See real verified KAYAK customer reviews for airlines flying from Chicago to Punta Cana. Airline scores are aggregated from all reviews left by passengers on KAYAK after flying with an airline. KAYAK doesn’t show reviews that are older than 5 years. Learn how KAYAK collects reviews.
Need help choosing which airline to fly with from Midway to Punta Cana? KAYAK airline reviews give an overall score for each airline based on loads of factors, including comfort, boarding, in-flight entertainment and more, to make your decision easier. See airline scores according to verified KAYAK customer reviews.
8.0
Alaska AirlinesOverall score based on 9201 reviews
8.2Boarding
7.3Food
7.3Entertainment
7.9Comfort
8.6Crew
Airline reviews

Crew was outstanding. Flight was fine. Food was a joke! I didn't get the priority I paid for!! That pissed me off since I paid extra!!!

8.0 Excellentjim, May 2024GEG - SAN
Read more about Alaska Airlines reviews

Crew was outstanding. Flight was fine. Food was a joke! I didn't get the priority I paid for!! That pissed me off since I paid extra!!!

I liked the price of the 2 way tix. I hated having to pay $8.00 for Internet access. It should be free. Legroom and seats are very confining.

I didn’t know that food needed to be ordered ahead. Please include this in the reservation information. Overall, very good experience.

Plane hit turbulence diverted to Houston. We'll probably get in after 3am

Cabin crew very friendly and pleasant. Flight left late but we didn't know why. Alaska Airlines app was not user friendly -- app wouldn't let us upgrade our seats, but no indication if flight was full. We wound up having to call the airline to request an upgrade and we were told none was available. Waste of time. Baggage retrieval was easy.

Full flight where I had another passenger sitting in middle seat who said that he had lost 250 lbs from 500. The stewardess on exiting the flight advise me that I was going to receive a refund. I thought she was talking about another passenger. The stewardess saw that to make him comfortable I had lifted the armrest and flew for 5 hours to Seattle from Reagan DCA with a portion of his body on my seat. I survived. I flight to remember!!!!

the flight was delayed almost 3 hours and not one time was we told that it was delayed or why. I had asked one of the crew members why it was delayed, 20 minutes after the flight was supposed to take off, and was told that they had no idea what was going on and that they had not been told anything. this is FRIGHTENING!!!! No excuse!!

Given incorrect gate upon check-in, corrected by the gate attendant, D6 rather than D5, minor inconvenience. As with the previous flight, passengers were admonished to voluntarily gate-check carry-on luggage with the statement that those in the last boarding group would have no choice but to do so. If the Boeing 737 MAX8/MAX9 doesn't have room for carry-ons it's an interior design flaw on the part of Boeing. Posting an advance warning would be helpful, such as "Boeing 737 MAX planes feature limited carry-on space. Please be aware." SFO's amenities and TSA much better than MCO's. Crew was amazing! Brought my own food because Alaska's onboard selection has soy in everything. Beverage service was excellent. This was the first and last trip with Alaska after the previous flight's issues. It's no reflection on the crew of this flight. They were great.

Flights were on time. Check in was fine. Crew members were pleasant.

The boarding gate is literally just an aisle to the concourse. There is no seating and it's shared with several other airlines. It's crowded, hot, and standing-room only. It's difficult to hear gate announcements over the PA system with too many other carriers crammed into a small space. I've enjoyed flying AA in the past on the west coast, but the BNA single gate experience is horrendous! Never again from BNA to SEA with AA.

I've flown many many times on Northwest and then Delta. The crew on this flight were absolutely the best I've had the pleasure of being looked after by.

Flew first class so everything was great. But maybe because the flights were red eye, no meals were served, just chips. I flew Alaska Air 1st class at 9PM (2 hour flight) and they served beef short rib sliders!

Had to change aircraft due to a faulty door. Surprisingly it only caused about an hour and a half of delay. Delta handled this situation as well as can be expected.

Awful. Flight was continuously getting delayed and gates kept changing without any reason. Flight was delayed for more then 3 hours

Paid premium for Delta only to be on safe but tired old 767 with ancient cabin in mediocre condition. Poor wifi and horrible inflight entertainment. Hardly a premium experience. Should have flown SW and had fun flight crew and no pretense

Our flight to Zurich was delayed by almost 3 hours, so we missed our next flight. There was no indication it would be delayed this much. We were told the gate had changed and then it apparently took over 2 hours to load the "catering" on the plane. We were not compensated in any way for the trouble.

Rated entertainment as Mediocre as there were major problems with the Infotainment system that took probably a half hour for them to fix.

Your crew could maybe answer the call bell at least one of the times I pressed it. I pressed it first time with 2.5 hours left in our flight bc my partner was hungry and wanted a sandwich. We finally got the sandwich with 40 mins left in the flight.

Half the bathrooms assigned to economy were out of action

Delta crushed it. Flight attendant in first was attentive and just never stopped. Honestly one of the best domestic flights I’ve been on.

It was delayed 9 hours for operational reasons, despite the plane arriving to the airport on time.

I am very disappointed with Frontier Airlines. They cancelled our flight because they couldn't find a crew member, and then didn't get us to our connecting flight. We had to cancel our whole vacation. We were promised flight and hotel vouchers, but they never sent them.

9hrs delay and didn’t provided anything until after flight landed $75 voucher for fiuture travel no meals or anything.

It was ridiculously hard to check in for the flight, and Frontier charged us a LOT of money to have a carry on suitcase, and then told everyone we could not carry on bags and had to check them through at the gate, and didn't refund the extra money we paid to have the suitcase as carry on.

I had a terrible experience with Frontier. I arrived before the 60 minute cut off and was told that Frontier has a two hour window for bags. I was then told the next available flight wasn’t until the end of the day (I had booked a 6am flight). I took a look around and saw other people being told that they could not board their flights or that they had to pay additional fees. I opted to rebook on American Airlines. There’s absolutely no straightforward way to contact Frontier, so this ticket was a complete waste of money. Oh - and the kicker is that the lady lied about the two hour cut off.

Frontier won’t help you at the airport without paying $25. Carry on was $75. Then you get on the plain and every beverage or snack is also a charge. Seats are hard and real packed in. I would never fly them again.

Worst experience I have seen. The flight was cancelled without any reason.

My experience with frontier staff at the Denver airport was absolutely horrible. The manager on duty was even worst if was the worst experience I have ever had, I have never been treated so poorly as a customer in my life! The staff was extremely rude, eye rolls and attitude and then refusal to help me at all. I wish I could never fly frontier again that’s how horrible it was!

The Frontier app wasn’t working. So I could not pay for a carry on the week prior to flying. They charged me 99$ at the gate to carry on a duffle bag.

Good for the price. My only complaint is that the pilot should keep the air flowing while passengers are waiting to getting out of airplane.

Book cheap flights from Chicago to Punta Cana

Recent one-way flight deals

 
Only flying one-way? Below are some of the best one-way flight deals from Chicago to Punta Cana found on KAYAK in the last 72 hours.
8/10Sat
1 stopFrontier
23h 02mMDW-PUJ
$104
6/15Sat
1 stopFrontier
22h 54mMDW-PUJ
$116
7/28Sun
1 stopFrontier
17h 42mMDW-PUJ
$126
9/16Mon
2 stops
16h 23mMDW-PUJ
$148
6/15Sat
2 stopsFrontier
22h 34mMDW-PUJ
$158
7/29Mon
1 stopFrontier
24h 26mMDW-PUJ
$164
8/10Sat
2 stopsDelta
17h 00mMDW-PUJ
$206
9/22Sun
2 stopsDelta
17h 37mMDW-PUJ
$250
9/22Sun
2 stopsDelta
17h 37mMDW-PUJ
$275
7/14Sun
1 stopDelta
6h 39mMDW-PUJ
$389

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Last minute flights from Midway to Punta Cana

Last minute flight, train and bus deals

 
These last-minute flight deals are the cheapest flights found on KAYAK in the last 72 hours for flights from Chicago to Punta Cana that are departing in the next 10 days.
6/4Tue
multi-stopFrontier
23h 38mMDW-PUJ
6/9Sun
multi-stopFrontier
11h 56mPUJ-MDW
$312
6/5Wed
multi-stopFrontier
26h 22mMDW-PUJ
6/9Sun
multi-stopFrontier
11h 56mPUJ-MDW
$313
6/4Tue
multi-stopFrontier
23h 38mMDW-PUJ
6/9Sun
multi-stopFrontier
11h 56mPUJ-MDW
$334
6/5Wed
multi-stopFrontier
18h 13mMDW-PUJ
6/9Sun
multi-stopFrontier
11h 56mPUJ-MDW
$367
6/4Tue
multi-stopFrontier
22h 04mMDW-PUJ
6/9Sun
multi-stopFrontier
11h 56mPUJ-MDW
$374
6/5Wed
multi-stopFrontier
23h 49mMDW-PUJ
6/12Wed
multi-stopFrontier
28h 04mPUJ-MDW
$380
6/5Wed
multi-stopDelta
6h 25mMDW-PUJ
6/10Mon
multi-stopDelta
7h 46mPUJ-MDW
$941
6/4Tue
multi-stop
26h 59mMDW-PUJ
6/9Sun
multi-stop
28h 51mPUJ-MDW
$995
6/4Tue
multi-stopDelta
18h 11mMDW-PUJ
6/9Sun
multi-stopDelta
9h 31mPUJ-MDW
$1,156
6/4Tue
multi-stopDelta
16h 54mMDW-PUJ
6/9Sun
multi-stopDelta
17h 35mPUJ-MDW
$2,424

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Chicago Midway Airport - Punta Cana Flights

Departure:

Chicago Midway Airport (MDW)United States

Destination:

Punta Cana (PUJ)Dominican Republic

Return flight deals:

Punta Cana - Chicago Midway Airport

Cabin classes: